In electrography, image charge patterns are formed on a support and are developed by treatment with an electrographic developer containing marking particles which are attracted to the charge patterns. These particles are called toner particles or, collectively, toner. Two major types of developers, dry and liquid, are employed in the development of the charge patterns.
In electrostatography, the image charge pattern, also referred to as an electrostatic latent image, is formed on an insulative surface of an electrostatographic clement by any of a variety of methods. For example, the electrostatic latent image may be formed electrophotographically, by imagewise photo-induced dissipation of the strength of portions of an electrostatic field of uniform strength previously formed on the surface of an electrophotographic element comprising a photoconductive layer and an electrically conductive substrate. Alternatively, the electrostatic latent image may be formed by direct electrical formation of an electrostatic field pattern on a surface of a dielectric material.
One well-known type of electrostatographic developer comprises a dry mixture of toner particles and carrier particles. Developers of this type are employed in cascade and magnetic brush electrostatographic development processes. The toner particles and carrier particles differ triboelectrically, such that during mixing to form the developer, the toner particles acquire a charge of one polarity and the carrier particles acquire a charge of the opposite polarity. The opposite charges cause the toner particles to cling to the carrier particles. During development, the electrostatic forces of the latent image, sometimes in combination with an additional applied field, attract the toner particles. The toner particles are pulled away from the carrier particles and become electrostatically attached, in imagewise relation, to the latent image bearing surface. The resultant toner image can then be fixed, by application of heat or other known methods, depending upon the nature of the toner image and the surface, or can be transferred to another surface and then fixed.
Toner particles often include charge control agents that desirably, provide uniform net electrical charge to toner particles without reducing the adhesion of the toner to paper or other medium. Many types of positive charge control agents, materials which impart a positive charge to toner particles in a developer, have been used and are described in the published patent literature. In contrast, relatively few negative charge control agents, materials which impart a negative charge to toner particles in a developer, are known.
Prior negative charge-control agents have a variety of shortcomings. Many charge-control agents are dark colored and cannot be readily used with pigmented toners, such as cyan, magenta, yellow, red, blue, and green. Some are highly toxic or produce highly toxic by-products. Some are highly sensitive to environmental conditions such as humidity. Some exhibit high throw-off or adverse triboelectric properties in some uses. Use of charge-control agents requires a balancing of shortcomings and desired characteristics to meet a particular situation.
The prior art discloses the use of 1,2-benzisothiazol-3(2H)-ylidene 1,1-dioxides as negative charge control agents for electrophotographic toners and developers. The general structural formula for this class of compounds is represented as: ##STR2## Such compounds are disclosed in U.S. Pat. Nos. 5,744,277, 5,719,001, 5,976,753, 5,821,025, 5,766,815, 5,714,295, 5,716,749, 5,750,715, 5,719,000, 5,723,249, 5,821,024, 5,922,499, and 5,739,235.
Of these disclosures, U.S. Pat. No. 5,922,499 is particularly notable. Disclosed are compositions with the general structural formula: ##STR3##
The compound 2-(1,2-Benzisothiazol-3(2H)-ylidene 1,1-dioxide)acetamide (I) has previously been reported (Melchiorre, Carlo, et al., Ann. Chim. (Rome) (1971), 61(6), 399-414). The method of synthesis utilized, however, is not useful for the preparation of the N-substituted amides of the present invention since the formation of the amide reported by Melchiorre requires the hydrolysis of a nitrile. This hydrolysis procedure can only lead to unsubstituted amides, according to the following reaction sequence. ##STR4##
It would be highly desirable to obtain negative charge control agents useful in electrostatographic toners and developers which agents have favorable charging and other relevant characteristics.